1. Field of the Invention
The present invention relates to a compound containing a diacetylene group in its molecule, which is useful as a starting material for photofunctional materials and highly rigid polymers, and a process for producing a polymer containing readily cross-likable diacetylene groups in its main polymer chain from such a compound.
The diacetylene compound can readily be converted to a polydiacetylene by topochemical polymerization of the diacetylene group and thus is useful as the starting material for various photofunctional materials.
Further, the polymer containing diacetylene groups obtained from the diacetylene compound of the present invention can be molded by a conventional method for molding polymers, and then the diacetylene groups can be cross-linked to obtain a densely cross-linked highly rigid shaped product having excellent thermal properties. Further, it can be molded together with an inorganic or organic filler, a pigment, an ultraviolet absorber, a stabilizer or the like, and the product is useful as a structural material.
Further, the product thereby obtained is cross-liked by .pi.electron conjugations, and, when doped, is useful as an electrically conductive material or a highly functional material such as a nonlinear optical material
2. Discussion of Background
As a compound containing a diacetylene group in its molecule, a number of compounds have been known wherein the neighboring-group of the diacetylene group is an aliphatic group. Further, with respect to a compound wherein the neighboring-group is an aromatic group, some compounds have been known wherein the aromatic ring is unsubstituted or substituted by an amino group, a nitro group or the like. (Gerhard Wegner, (Polymer Letters), 9, p.133-144 (1971); Barbara Grant, (Mol. Cryst. Liq. Cryst.), 48, p.175-182 (1978)).
It is well known that among these diacetylene compounds, certain diacetylene compounds undergo polymerization of the diacetylene groups in their crystal state by heat or high energy rays such as .gamma.-rays or ultraviolet rays (topochemical polymerization). (G. Wegner, Z. Naturforschg., 246, p.824 (1969); G. Wegner, Makromol. Chem., 134, p.219 (1970); G. Wegner, J. Polym. Sci., 89, p.133 (1971)).
With respect to these diacetylene compounds, many researches have been conducted concerning their topochemical polymerization and application of the topochemical polymer to photofunctional materials or the like.
However, there have so far been only a few research reports on a polymer containing a diacetylene group in the main polymer chain. (Makuromol. Chem., 134, p.219 (1970) and J. Polym. Sci. Polym. Chem. Ed., 19, p.1154 (1981)).
There has been no attempt to develop a polymer capable of isotropically providing a high modulus of elasticity by subjecting a polymer containing diacetylene groups to the three-dimensional cross-linking reaction.
The present inventors conducted extensive researches to make use of the high reactivity of diacetylene groups to obtain the shaped product having isotropically high rigidity and excellent heat resistance, and they found that a highly rigid shaped product could be obtained by molding a polyester or polyurethane containing diacetylene groups in its solid phase at a temperature below the decomposition temperature or melting point thereof under a high pressure condition. (U.S. Pat. No. 4,654,178).
However, the polymer containing diacetylene groups produced from the diacetylene compound having an aliphatic group as the neighboring-group of the diacetylene group, has the limitation in its heat resistance, and no shaped product having fully satisfactory properties has been obtained yet. Therefore, it is desired to develop a material capable of providing a shaped product having higher rigidity and improved heat resistance.